One-pot anodic lactonization of Fenchone and Menthone and electrosynthesis of a new magnolione analogue

Batanero, Belén; Recio, Javier; Barba, Fructuoso

doi:10.1016/j.elecom.2016.02.018

Cited by 4 publications

(4 citation statements)

References 12 publications

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“…Consequently, the synthesis of bridged [2,2,1] bicyclic lactones received wide attentions and several approaches have been developed. The typical methods include Baeyer–Villiger oxidation 6 , esterification 7 , 8 , halolactonization 9 , 10 , electrocatalytic reaction 11 , and others 12 – 14 . However, most of these approaches focused on the synthesis of racemic bridged [2,2,1] bicyclic lactones and multistep synthesis was necessary to achieve these transformations.…”

Section: Introductionmentioning

confidence: 99%

A concise access to bridged [2,2,1] bicyclic lactones with a quaternary stereocenter via stereospecific hydroformylation

et al. 2021

Nat Commun

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Chiral bridged [2,2,1] bicyclic lactones are privileged structural units in pharmaceutics and bioactive nature products. However, the synthetic methods for these compounds are rare. Here we report an efficient method for enantioselective construction of bridged [2,2,1] bicyclic lactones bearing a quaternary stereocenter via Rh-catalyzed asymmetric hydroformylation/intramolecular cyclization/pyridium chlorochromate (PCC) oxidation. By employing a hybrid phosphine-phosphite chiral ligand, a series of cyclopent-3-en-1-ols are transformed into corresponding γ-hydroxyl aldehydes with specific syn-selectivity. Then, hemiacetals form in situ and oxidation with PCC in one-pot affords bridged [2,2,1] bicyclic lactones in high yields and excellent enantiomeric excess. Replacing the hydroxyl group by an ester group, cyclopentanecarbaldehydes with a chiral all-carbon quaternary stereocenter in the γ-position can be generated efficiently.

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Section: Introductionmentioning

confidence: 99%

A concise access to bridged [2,2,1] bicyclic lactones with a quaternary stereocenter via stereospecific hydroformylation

et al. 2021

Nat Commun

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“…An oxidative couple in monosaccharide was reported at 0.65 V and corresponded to the first one‐electron transfer . Anodic lactonization of cyclohexanones was suggested to be an irreversible two‐electron transfer reaction, and the observed oxidative couple at 0.65 V could suggest the first electron transfer peak. Lactonized trimer 4 could not be formed with working currents 10 and 20 μA at pH 5, and the potentiostatic curves were recorded between 0.9 and 1.1 V (Figure c).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical lactonization of trisialic acid

Chen

Lee

2018

J Chinese Chemical Soc

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A sensitive method using high‐performance capillary electrophoresis (HPCE) is employed to study the electrochemical lactonization of α2,8‐trisialic acid. Analysis shows that the sialyl lactonization of trisialic acid in an acidic aqueous solution (pH 4.2–6) is highly enhanced by a supporting electrical current (30–100 μA). CE results indicate that this electrochemical lactonization with a supporting current is faster than the acid‐catalyzed lactonization in acetic acid. This acceleration in the reaction suggests that the acidity increases close to the Pt electrode and assists the sialyl lactonization during electrolysis. Three lactone species of trisialic acid formed in the acidic aqueous solution were detected with HPCE, and the fully lactonized species were examined with time‐of‐flight mass spectrometry and NMR spectroscopy. The elution order of the lactone isomers obtained from previous report and from this study together reveals a regioselective lactoziation in which the sialyl residue close to the reducing end was more reactive than that close to the nonreducing end.

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“…Electrosynthesis is considered a clean and efficient synthetic methodology. When using the electron as a reagent, the number of steps is reduced as compared to conventional thermal processes, cleaner reaction mixtures are obtained, the isolation of the product is simpler, and the pollution caused by the use of chemicals is decreased. − Stimulated by the recent achievements in electroorganic synthesis, in this work we study the electrochemical reduction of ISH in N,N-dimethylformamide (DMF) solution at a preparative scale (see Supporting Information) as a new and clean methodology for NMI synthesis. The electrolysis (controlled potential electrolysis, CPE) was performed under different experimental conditions (Table ).…”

Section: Introductionmentioning

confidence: 99%

Electrosynthesis ofN-Methylisatin

et al. 2019

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Isatin in a solution of dry N,N-dimethylformamide/NaClO4 is electroreduced in the presence of CH3I. N-methylisatin (NMI) is obtained in quantitative molar yield and high current efficiency by controlled potential electrolysis (CPE). NMI and N-methylisatoic anhydride are the reaction products when CPE is performed in the absence of CH3I, but adding it once the CPE was completed. The water effect on the identity and yield of the reaction product(s) is investigated. Reaction pathways are proposed.

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One-pot anodic lactonization of Fenchone and Menthone and electrosynthesis of a new magnolione analogue

Cited by 4 publications

References 12 publications

A concise access to bridged [2,2,1] bicyclic lactones with a quaternary stereocenter via stereospecific hydroformylation

A concise access to bridged [2,2,1] bicyclic lactones with a quaternary stereocenter via stereospecific hydroformylation

Electrochemical lactonization of trisialic acid

Electrosynthesis ofN-Methylisatin

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